


The Way You Look Tonight

by hannahindie



Category: Supernatural
Genre: Dean Winchester - Freeform, F/M, Reader Insert, Sam Winchester - Freeform, Supernatural - Freeform, dean being a sneaky monkey, maybe some present sam x reader, past sam x reader - Freeform, sam in a tux, spn fanfic, supernatural fanfiction - Freeform
Language: English
Status: Completed
Published: 2018-12-12
Updated: 2018-12-12
Packaged: 2019-09-17 04:53:02
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,286
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16968036
Author URL: https://archiveofourown.org/users/hannahindie/pseuds/hannahindie
Summary: Dean ropes Sam into a hunt under the guise that he could get all the free, fancy food he wanted. Sam agrees to go, but regrets it the moment he sees who he’s meeting…and she’s not too pleased either.





	The Way You Look Tonight

“We’ve got a job.”

Sam looked up from his laptop as Dean tossed a newspaper on the table in front of him. He raised an eyebrow, “And?”

“And,” Dean said as he tapped the paper, “it’s not that far from here, and it’s _catered_. You heard me, _catered_. C’mon, it’ll be easy. Cursed object, fancy auction, even fancier food, just like the old days, Sammy.”

Sam carefully closed his computer and leaned back in his chair, “This never ends well for me, and you know it. The last time, my date was an old woman who didn’t understand personal space or the word no while _you_ got to run off with the Bella.” Sam shuddered at the thought, “No thanks, hard pass.”

“I said I was sorry about that. Come on, I’ll let you have the girl this time. I know, we can call Y/N! We haven’t seen her in awhile. You two can get us inside, and then I’ll do my thing. And have some of those delicious crab rolls they always serve at these things.”

Sam stood, shaking his head as he collected his things, “First of all, there’s a reason we haven’t seen Y/N for awhile. She’s not going to agree to it if it’s me, and honestly, I don’t really want to. Call Garth, see if he can get someone to cover it.” He pushed his chair in and started to walk away.

“What if I can get Jody to meet us? Will you do it then?” Dean practically whined and Sam stopped and dropped his head in defeat, his back towards his brother.

“Fine. If you can get Jody to go, I’ll do it.”

Dean grinned, “Awesome.”

“I hope your crab rolls are worth it,” he mumbled as he resumed walking towards his room. 

Dean waited for Sam to disappear down the hall, then pulled his phone from his pocket and dialed as he wandered towards the kitchen.

_“Hello?”_

“Hey, it’s Dean. What’s up?”

There was a long pause, then a hesitant response, _“Nothing…why?”_

“You mean I can’t just call my favorite hunter and shoot the shit, huh?”

_“Dean, you haven’t called me in weeks. I haven’t seen you in, like, three months, and for once it wasn’t because you were in purgatory, or hell, or wherever it is your dumb ass usually ends up. So no, you can’t just call and shoot the shit.”_

“Y/N, listen, I’m sorry. It’s been…it’s been busy. Nothing you needed to be mixed up in, trust me, you’d thank me. But I found something pretty straight forward, and it’s not too far from the bunker. I was hoping you could help with it. You’d get to get all dressed up, fancy free food…the whole nine.”

_“Something simple, huh?”_

“Yea, yea, just a quick crash and grab. There’s a cursed object, silent auction, yada yada yada. C’mon, I miss you. Let me take my favorite girl out on the town.”

Y/N laughed, _“You’re an idiot, Dean Winchester. There is a hint of bullshit surrounding this that smells faintly like eau de Samuel.”_

“Oh, come on. He’s not even going to be there, he’s taking off to go see some movie with subtitles that’s, like, five hours long. You know you wanna spend time with your favorite Winchester.”

She sighed, _“It doesn’t take much to be the favorite, you know. I wouldn’t be too proud of yourself.”_ There was a moment of silence as she thought about her decision, and Dean began to think maybe his little plan wasn’t going to work after all. _“Okay, fine. But you’re going to show me a damn fine time, okay? You will retrieve whatever snack or boozy beverage I want, and you won’t complain. Capiche?”_

“Yes, ma’am.” Dean smiled to himself; this had been too easy. “Do you still have that dress from the job we did in Boston?”

_“Yes…why?”_

“Like I said, this is real fancy, gotta fit the part, right?”

_“I’m going to regret this. Send me the time and the address.”_

“Will do. See you soon, Y/N.” The line went dead, and Dean shoved his phone back into his pocket, a smug look on his face.

Nailed it.

* * *

“Here.” Dean slipped an earpiece to Sam, and Sam rolled his eyes.

“What is this?” He rolled it between his fingers, trying to figure out where Dean had even procured the small, flesh colored electronic.

“It’s an earpiece. How else am I supposed to know the coast is clear for me to sneak into the auction hall?”

Sam rolled his eyes as he put it in, “You’ve been watching way too much James Bond.”

Dean grinned, “Maybe I’ve been watching just enough.” He cleared his throat, “By the way, Jody had to pull out last minute. I got a replacement, she should be here somewhere.”

Sam looked at Dean sharply, “What? Who is it?”

Dean shrugged, “You’ll know who it is when you see her.” Dean looked over Sam’s shoulder, then nudged him, “Take a deep breath, you only need one shot. Make it count.“

Sam’s eyebrows furrowed, “Did you just quote Quantum of Solace at me?”

Dean shook his head, “Who’s the one that’s been watching too much James Bond?” He nodded in the direction of the bar, and Sam turned around.

_That dress._ He would have recognized it anywhere. The crimson silk draped low in the back, showing off the gentle slope of smooth shoulders and two little dimples at the base of her spine. Sam knew before she even turned around how the neckline plunged nearly to her waist, the slick fabric caressing every curve, how it covered just enough to make his heart race and something in his gut tighten.

“Dammit, Dean,” he hissed, turning to find his brother long gone. He turned back and straightened his jacket. _“Might as well get this over with,”_ he thought to himself as he began walking towards her. Just as he reached the halfway point, she turned, and it felt like his heart had jumped into his throat. The narrow slit that ended mid-thigh dropped open as she shifted, her long leg exposed as his eyes traveled down to her five inch black heels, the straps crisscrossing to just above her ankle. He looked back up just in time to see her face as she realized who she was actually meeting.

_Dammit, Dean.  
_

* * *

Y/N sipped the champagne the passing waiter had offered her and tried to pay attention to the businessman that was attempting to impress her with…whatever it was he was talking about. She’d lost interest five minutes ago, but he seemed nice enough and, as per usual, Dean was late. She discreetly looked at her phone and sighed; he should have been here twenty minutes ago. She smiled politely at the man whose name she had already forgotten, “I’m sorry, I need to use the ladies’ room, if you’ll just excuse me for a moment.” The man, though obviously disappointed, gave her a tight lipped smile and turned back to the man he’d been talking to before Y/N had caught his attention.

She turned to walk away and immediately froze as her gaze landed on the last person she had expected, or wanted, to see. Sam was standing right in the middle of her path to the bathroom, his eyes wide when they locked with hers. They stared at each other for what felt like an eternity, and for a moment she forgot why they hadn’t spoken to each other in three months, or why she had moved out of the bunker in the first place.

Sam looked good on a normal day, but when he dressed in a tux, it was like all the oxygen was sucked from her lungs. Today was no exception. His long, chestnut hair had been swept back hastily, a few messy, out of place locks tempting her to tuck them behind his ear. She wondered if he’d finally broken and bought a tux; there’s no way a rented one would have fit so perfectly. She’d forgotten how broad his shoulders were, and how he towered over practically everyone around him.

She took a deep breath and walked towards him, “Sam, what the hell are you doing here?”

“I could ask you the same thing,” he responded as his eyes traveled down her body and back up. As irritated as she was, a chill ran through her at how he looked at her, his bottom lip tucked between his teeth.

“Quit looking at me like that,” she hissed quietly as she pulled him off to the side. “I was supposed to be meeting _Dean_ , not _you._ This was…we…I can’t…” she stuttered, her arms crossed as she scowled at Sam.

He frowned, “Listen, you’re not the only one that wasn’t expecting this. I was supposed to meet Jody.” They stared at each other in silence for a moment before Sam cleared his throat, “Listen, it’s too late now. Dean is already trying to get into the auction room and grab the doll, and we need to make sure no one goes in there while he’s doing it, okay?”

She rolled her eyes, “Of _course_ it’s a cursed doll. Because what else could make this evening worse?” She looked around the room before spotting the hall that led to the auction room. “What’s your plan for distracting people from going in there?”

“You’re not going to like it.”

“Sam, I don’t like this _anyway_. Out with it.”

“Okay, but don’t smack me.”

Before she could respond, Sam grabbed her by the waist, one hand staying there while the other slid down her arm and grasped her hand. He leaned in close, his breath tickling the shell of her ear as he whispered, “Can you at least pretend to like me?” She swallowed thickly as she moved her arms and draped them over his shoulders, her hands locking loosely behind his neck. “Thank you. Now…what is the one thing that makes people most uncomfortable in public?” he asked as they danced slowly across the room and through the crowd.

Y/N pulled back and looked at him in confusion, realization dawning on her when he raised an eyebrow. “Sam, no-”

“It’s just a job, Y/N. Not a big deal. We do this, we move on. Well, we kill Dean, _then_ we move on.”

“Was this the plan for Jody, too?” she asked, trying to contain her laughter as Sam blushed.

He shrugged, “Sometimes you have to adapt the plan.” He leaned in again and his lips brushed her jaw, “Just tell me if you get uncomfortable. We just have to do this long enough for Dean to get in and back out.”

She cleared her throat, “Yea, fine. I’ll let you know.” They continued to dance across the floor and towards the hallway leading to the auction room. She was disappointed when Sam pulled away and grabbed her hand instead, dragging her into the narrow hall.

“I think it’s room 109…here it is.” He stopped and turned back to face her. She gasped as he grabbed her roughly by the waist and pushed her backwards, the wall cool against her bare back. His lips brushed hers, and she could feel them shaping his words as he whispered against her, “Remember, tell me when to stop and I promise, I will.” Instead of answering, she pressed herself against him, her lips crashing into his desperately. She had forgotten how warm he was, how soft his lips were and how perfect he fit with her. The months of anger and frustration melted away as her hands explored the wide expanse of his chest. One of his hands moved up and into her hair, digging into her previously perfect updo and twisting her locks around his fingers. She groaned into him, and she felt him smile.

“Sam…” His lips were like fire as they settled on her soft skin, his teeth nibbling gently at her pulse point. His hands were everywhere; on her hips, in her hair, caressing her through the thin silk of her dress. She sighed as he pulled away, his eyes dark and his lips kiss swollen.

“Are you okay?” he asked gently, the sharp edge in his gaze turning into gentle concern as he searched her eyes to make sure she was giving him an honest answer.

“Yea, I’m….I’m fine.” She sighed, “I’m sorry, Sam. I shouldn’t have left. I know how hard it is for you and Dean to…to just let things happen. I should have fought for it, I should have fought for _us_. I’m just…I’m so sorry.”

He cupped her cheek gently, his palm rough against her soft cheek and she leaned into it, her eyes closed. “You don’t have to apologize for anything. I was wrong, and I should have gone after you. I just…I thought it would be better for you if I just let you go. Winchester logic, I guess.”

She smiled and opened her eyes to find his hazel ones staring at her, “Yea…you Winchesters and your self sacrificing ways. As if you don’t give up enough for this life.” She brushed hair from his face then reached back and pulled the bobby pins from her own, shaking out her hair in messy waves. Sam raised an eyebrow, and she grinned, “We gotta sell it, right?” She winked, and Sam chuckled.

“With the way you look tonight, it’s not going to be a hard sell.”

She opened her mouth to reply and he interrupted her with a kiss, “Don’t cheapen the moment, Y/N.”


End file.
